Caitlin & Rob
Things To Do
Ruse
This beautiful restaurant just opened this summer and gives its visitors a delicious taste of the local cuisine!
Golf, Tennis, Bikes, Water Activities at the Inn at Perry Cabin
The Inn at Perry Cabin has everything you need to enjoy the area! You can rent bikes, reserve a slot for tennis or golf, explore the waterfront on a chartered sailboat. Visit the website or call the Inn to learn more!
Foxy's Harbor Grille
Foxy's is right on the waterfront and one of our favorite places to enjoy an orange crush and a basket of crab claws while listening to live music performed by local musicians!
Inn at Perry Cabin Pool, Spa & Fitness Center
Relax and enjoy the Inn's beautiful infinity pool, 24/7 fitness center, group fitness classes, or spa treatments!
Corah's Corner
Corah's just opened in 2020 and is an awesome place to enjoy yummy food and live music!
St. Michaels Marina
Our favorite thing to do at the Marina is rent a Gem Car (a small, 2 and 4 seat street electrical car) to cruise around town. We also love shopping at the cute Marina shop and picking crabs at the Crab and Steak house.
Bistro St. Michaels
This French bistro right on main street is one of our favorite spots for brunch!
Chesapeake Bay Maritime Museum
Explore the sights and visit the Maritime Museum. Located right on the water, the museum is a great place to learn about the history, environment, and culture of the entire Chesapeake Bay region.
Ava's Pizzeria & Wine Bar
This is our favorite pizza spot in town. Stop here for lunch or dinner to enjoy the casual vibe and great food and wine!
St. Michaels Winery
The wine tasting room on the main street is a fun and inexpensive way to explore the tastes of St. Michaels! No reservations are required, so pop in anytime from 11AM to 6PM for $1 per sample of wine!
The Crab Claw
Stop by the Crab Claw to pick some crabs for a traditional Maryland-er experience!
Eastern Shore Brewing
Enjoy a flight of beer at the oldest brewery on the Eastern Shore! Sample any of the 10 beers on tap at this local brewery right on main street that boasts a wooded Eastern Shore vibe.
Limoncello Restaurant & Wine Bar
Visit Limoncello to enjoy a taste of Italy! This is a great dinner spot founded by two Naples, Italy natives committed to bringing authentic Italian cuisine to the Eastern Shore.
Shore Pedal & Paddle
Weather permitting, rent a kayak, bike, or stand-up paddleboard to get out on the water and further enjoy the beauty of the Chesapeake Bay!
Blue Heron Coffee
Start your morning right with Blue Heron's locally roasted coffee at our go-to coffee spot in town!
Shops on Talbot Street
There are tons of cute shops in town on the main street of St. Michaels, Talbot Street. Head to town to shop anything from local art, clothing, gifts, antiques, and more!
208 Talbot
Great spot for dinner with American style food!
JoJo's Cupcakes & Cream
Whenever we come to St. Michaels, we always stop at Jojo's for one of their beautiful decorated cupcakes or tasty homemade ice cream.
Experience St. Michaels
Visit the Experience St. Michaels website to learn about everything St. Michaels has to offer!